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In the information-is-free age, the notion that writing is a skill deserving of financial compensation has begun to seem radical. So when writers do hit a big payday, the rest of us should look up from our keyboards and cheer. That's the sound you heard from my office this week when 26-year-old Lena Dunham, creator of the HBO show Girls and the film Tiny Furniture, was reportedly given an advance of $3.5-million for an advice book.

But I think my rah-rah might have been drowned out by a resounding media guffaw. "Is Lena Dunham's advice book worth $3.5-million?" read a headline in the online publication The Week, while Newser declared the advance "A Big Problem." Meanwhile, Random House issued a gushing release promising a book of personal essays "in the tradition of Helen Gurley Brown, David Sedaris, and Nora Ephron" (no pressure, Lena). The New York Times ran a few lines from Dunham's 66-page proposal, where she writes: "Red lipstick with a sunburn: How to dress for a business meeting and other hard-earned fashion lessons from the size 10 who went to the Met Ball."

Unfortunately, that sentence flags the thing that has made Dunham such a divisive figure in the blogosphere, and part of the reason her advance causes knee-jerk ire. Random House may be pegging her as the voice of a generation (a joke she's made on Girls), but who exactly does she represent? Girls unfurls in privileged corridors, following the New York City shenanigans of white 20-somethings on the mommy-daddy bankroll whose problems involve book launches and bad sex. Dunham plays the show's star, Hanna, as endearing but maddening, fumbling through early adulthood. Her bad judgment drives each episode.

Those who don't like it condemn Girls's social narrowness, and those same critics will inevitably note that most 26-year-olds aren't struggling with what to wear to the Met Ball; Dunham's experience is an anomaly born of entitlement. In part, this is true: Dunham's parents are well-known, well-connected New York artists. When Nora Ephron died, Dunham wrote an appreciation, as did many writers – only not in The New Yorker. Nor did most writers recount bringing brownies to a dinner party at Ephron's apartment.

But there's room for these kinds of stories. Her perspective is wry and sufficiently unique to serve as a welcome counter to most 20-something women depicted on TV. I will always choose Girls's comic myopia over the lazy racism of 2 Broke Girls or the inanity of The Bachelor. Beneath the relationship foibles, the true target of Dunham's humour is, in fact, the inequality and obliviousness she's been chided for.

Hers is a slightly immoral, prickly persona and perhaps the lack of on-screen likeability makes her off-screen success more galling. Louie CK, similarly misanthropic and self-involved, has been roundly applauded for the millions he's made selling his concerts online. The loathsome male – Seinfeld, Larry David, Woody Allen – is comedy gold, but the loathsome female appears to be a tougher sell.

Perhaps it's where the loathing is located. Dunham upends expectations by rarely making her body, which is a nicely average human shape, a punchline. On Girls, she often appears naked or minimally clothed, and was much mocked for showing up recently at an event without pants (she wore shorts under a long top). She didn't apologize: "My response is, get used to it because I am going to live to be 100, and I am going to show my thighs every day till I die." This feels like a generational switch: Female comedians have often been encouraged to make their bodies, sexy or fat, the joke. Even Tina Fey's Liz Lemon resorts to Cathy-style gags about her hips. But Dunham is of a different, perhaps more confident, generation, and she doesn't plumb physical insecurities for laughs, going – like a lot of male comics – for the psyche instead.

Yet Dunham does have a large audience, with more than 372,000 Twitter followers and an Emmy-nominated show recently renewed for a second season. It's not so crazy that a publisher would want her to pen a new model Bossypants, a book, for which Fey was reportedly paid $6-million.

The sheer size of Dunham's advance at a much earlier stage of her career invites investigation of her "worth." For better or worse, however, "worth" is subjective when it comes to compensation. If we were dispensing salaries according to the greater social good, then teachers would be earning more than Ryan Seacrest and garbage men would take home as much as those striking NHL players.

The 1995 book The Winner Takes All Society, posits that modern markets, more than ever, reward the top few "superstars" over everyone else. The past three decades have borne out the prescient thesis of authors Robert H. Frank and Philip J. Cook to an alarming end: While the highest paid CEOs have collected huge wages and bonuses, salaries below the top level have stagnated or declined. Whether you're in the 99 or the 47 per cent – I guess that's almost all of us – it kind of sucks to hear about a $3.5-million payout for anyone.

The last time a big literary advance made headlines was in 2011, when Chad Harbach's novel The Art of Fielding was sold for a reported $650,000. Harbach had been working as an unpaid editor at the literary magazine n+1, and he'd had to move back into his (not famous) parents' house when the book he'd toiled over for nine years finally sold. Harbach fulfills the romantic narrative of the self-made artist who paid his dues – someone "worth" the excess. Dunham's story may be different, but in this climate, a well-paid writer – or worker – is its own kind of happy ending.